2-Nitrobenzenesulfonyl chloride → Ethyl 7,7-dimethyl-5-(2-nitrophenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate

HRID 468671Notes

Reaction equation

HRID 468671 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][NH:6][CH2:5][C:4]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:10][C:3]1=2.CCN(C(C)C)C(C)C.[N+:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35](Cl)(=[O:37])=[O:36])([O-:28])=[O:27]>C(Cl)Cl>[CH3:1][C:2]1([CH3:16])[CH2:7][N:6]([S:35]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N+:26]([O-:28])=[O:27])(=[O:36])=[O:37])[CH2:5][C:4]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:10][C:3]1=2

Participants

5

Reactant 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66931742Ethyl 7,7-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate

Product 1

HCID 66932174Ethyl 7,7-dimethyl-5-(2-nitrophenylsulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 7,7-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate (20.5 g, 0.074 mol) and DIPEA (42.8 g, 0.37 mol) in DCM (400 mL) was cooled to 0° C. 2-nitrobenzene-1-sulfonyl chloride (17.3 g, 0.078 mol) was then added and the reaction mixture was allowed to warm to room temperature overnight. The crude reaction solution was applied directly to a silica gel column and purified (10-20% EtOAc/hexane) to afford product (27.6 g, 88%). 1H NMR (400 MHz, CDCl3) δ 7.98 (dd, J=4.8, 2.4 Hz, 1H), 7.64-7.68 (m, 2H), 7.57 (dd, J=4.4, 2.4 Hz, 1H), 7.37 (s, 1H), 7.19 (s, 1H), 4.33 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 3.33 (s, 2H), 1.31 (s, 6H), 1.19 (t, J=7.2 Hz, 3H),

Workup

  1. customThe crude reaction solution
  2. custompurified (10-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-95ef17c0f2d1468e962afe0c957ad21e
Source dataset
uspto-grants-2014_01
Patent number
US08624040B2

Reaction notes

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